1918 Inverted Jenny

The Inverted Jenny (also known as an Upside Down Jenny or Jenny Invert) is a 24 cent United States postal stamp that was first released on May 10, 1918, and has an upside-down image of the Curtiss JN-4 airplane in the middle of the design; it is the most famous blunder in American philately. Only one pane of 100 inversion stamps was ever discovered, making this misprint one of philately most expensive rare postage stamps.

Apart from having the biplane printed backwards, the inverted Jenny is well-known for numerous reasons. One of the first buyers of these inverts, Benjamin Kurtz Miller, paid $250 for the stamp. Miller's inverted Jenny, sheet position 18, was stolen in 1977 but found in the early 1980s, albeit the top perforations had been chopped out, making it impossible to identify as the stolen Miller stamp. The stamp was mutilated to appear as if it came from the top row of the sheet, and Klein's numbering on the back was accordingly tampered with to disguise the stamp as position 9—an astute piece of deception based on the knowledge that position 9 had never appeared on the market: in fact, the real position 9 emerged decades later as the locket copy.

An unknown internet bidder paid $1.593 million for the minuscule piece of history, plus an 18% buyer's fee. An excellent Inverted Jenny previously sold for $1.3 million in 2016.

Price: $1.593 million